The Enterprise offers the Douglas community a wide array of opportunities to attend events, promote their business and improve the community. Look through the below, or give us a call, to learn more.

JACKALOPE DAYS, June 6-9, 2024

aa at JackaJoin us for the 2024 Jackalope Days Celebration, June 6th-9th!

Jackalope Days is a community celebration, with many entities and clubs coming together to put on a one-of-a-kind party for YOU! This 4-day event will have something for everyone, you’re not going to want to miss it!

Thursday, June 6th:

  • PARK IT! At the Douglas Railroad Museum from 5pm-8pm

Friday, June 7th:

  • Railroad Day at the Douglas Railroad Museum from 11am-3pm
  • Chalk Fest at Jackalope Square from 10am-12pm
  • Book Crawl from the library to local book shops 12pm-5pm

Saturday, June 8th:

  • OECC Ride, Row, Run at the Wyoming State Fairgrounds from 7am-12pm
  • Annual Boys & Girls Club Pancake Breakfast at the Moose Lodge from 8am-10am
  • Laramie Peak Humane Society Low Rider Dog Races at the Jackalope Square Alleyway starting at 8:30am
  • Vendor Fair at Jackalope Square from 9am-2pm
  • Youth Lemonade Stand Contest at Jackalope Square from 9am-2pm
  • Live Music by the Wyoming Wayfinders at Jackalope Square from 11-2
  • Chalk Fest & Bouncy Castles at Jackalope Square from 11-2pm
  • Classic Car Show on 2nd Street from 11-3pm
  • 4th Annual Bed Races start at 12pm
  • LaBonte Street Dance starts at 8pm

Sunday, June 9th:

  • Community Church at Jackalope Square (more information coming)
  • Memorial Hospital of Converse County Block Party & Enterprise Community Awards in MHCC Parking Lot starts at 6pm

CLICK HERE to stay up to date on Jackalope Days

Jackalope Days Vendor Form

Bed Races Registration Form & Bed Races Waiver (both must be filled out)

Youth Lemonade Stand Contest, June 8, 2024

Do you know a young entrepreneur ready to make a SPLASH?

Main Street Douglas encourages the youth to compete in 2024 Youth Lemonade Stand Contest during the Jackalope Days vendor fair on Saturday, June 8th, at Jackalope Square, from 9am to 2pm!

This is a fun way to help the youth build confidence, learn responsibility, be creative, and establish a good work ethic. As this contest evolves into Main Street Douglas’ future YELP (Young Entrepreneurs Leadership Program) it will also provide youths the opportunity to learn about money management and goal-setting.


  • Register by the JUNE 1st DEADLINE! Forms available HERE
  • Build/create a stand or booth to sell lemonade
  • Registration is open to youth 17 and younger or youth organizations such as FBLA, 4-H, Church Youth Groups, Interact,  and more!
  • Provide your cups, napkins, garnish, etc., and feel free to include a tip jar
  • Set up your stand/booth at the Jackalope Days Vendor Fair (designated area)
  • Manage your lemonade stand and serve your best lemonade
  • Single or multiple youths can work together to operate the stand
  • Each booth will present their lemonade to the judges one at a time (judges will get free samples)
  • Lemonade tasting and presentation will be scored on a point system, rubric included
  • Compete against other peers to win prizes!
  • Parental permission required

For more information, contact Briana Gallup at or Jen Goodwin at

Information, Rules, Prizes, Registration, and Judging Rubric available HERE

Douglas Community Awards

Join us Sunday, June 9th, at 6pm for the Douglas Community Awards!

The Douglas Community Awards are a tradition to honor those who serve the community. The Ceremony honors 11 categories per year, and this year the Enterprise will be partnering with Memorial Hospital of Converse County’s Block Party!

This year we are looking for nominees in the following categories:

  • Citizen of the Year
  • Outstanding Leader
  • Volunteer(s) of the Year
  • Most Improved Business of the Year
  • Service to the Community
  • Educator of the Year
  • Business of the Year
  • Youth Citizen of the Year
  • Start-Up Business of the Year
  • Event of the Year
  • Create Your Own Category

Take a moment to nominate someone who has made a difference in your life or the community this year and join us Sunday June 9th at 6pm! 

Nomination Forms Available HERE

First Responders Freedom Fest & 5k

The annual Independence Day Celebration in Jackalope City is brought to you by the Douglas Police Department and the Enterprise, along with other volunteers, to bring family fun, games, kiddie parade, and 5k to Washington Park on July 4th. 

ALL ACTIVITIES WILL BE AT WASHINGTON PARK. Kiddie Parade registration and parade route start at Jackalope Square, 5K Fun Run registration will be at Washington Park, with route through the cemetery.

    Get your 5k registration forms HERE

    Get your parade registration forms HERE

    PARK IT! at the Douglas Railroad Museum

    First Thursdays starting May 2nd, 2024, we will be hosting PARK IT! Food Truck and Vendor Festival from 5pm-8pm.

    Enjoy the nice weather, stay and enjoy or take your food to go!

    PARK IT! Events will be May 2nd, June 6th, Aug 1st & Sept 5th in 2024.

    Are you a vendor and want to join the fun? Sign up today!

    Wyoming State Fair Parade

    The Wyoming State Fair Parade is a long-held tradition in the Cowboy State. Whether you create an entry or float or come to watch, we hope you will join us for family fun in downtown Douglas.

    The 2024 parade theme is, “WYld & Wooly.” There is a $25 entry fee for General/Classic Cars/ Wagon Entries, $15 entry fee for Youth and Nonprofits ($40 for late entries) and entries are due Aug. 10th.


    Jackalope City Farmers Markets take place on Saturdays in August and September. Sign up today!

    You’ll find more than your veggies at the Jackalope Square Farmers Market. There are baked goods, creations, self-care products and more. If you would like to be a vendor, fill out the below application.

    Farmers Market Vendor Form HERE

    Apply for a FACADE GRANT

    As individual businesses improve, so too, does our community as a whole. The Enterprise manages a special matching funds grant to help business owners improve their storefront, the first impression visiting customers get of your store or business. Download the application for more information.


    Be a Vendor at COWBOY CHRISTMAS

    Each November, The Enterprise hosts Cowboy Christmas at the Wyoming State Fairgrounds. Again in 2024, the event will be two days, opening on Friday evening and spanning through Saturday afternoon. Sign up early– space is limited! 



    Get out your best chili recipe! November 23, in conjunction with Cowboy Christmas, Main Street Douglas will host the Fire on Main Street Chili Cook-Off. Proceeds from the event support downtown Douglas projects and activities. If you’re not a chef, consider coming and sampling the year’s entries. Deadline to sign up for competition is Wednesday Nov 20, 2024.


    Fire on Main Street Chili & Food Product Rules